# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_230511lu_lgpz086225_l2_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2gl7r2
_database_code_depnum_ccdc_archive 'CCDC 2281654'
loop_
_audit_author_name
_audit_author_address
'Jiabin Shen'
; Zhejiang Shuren University,
China
;
_audit_update_record             
;
2023-07-14 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2023-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O'
_chemical_formula_sum            'C19 H16 N2 O'
_chemical_formula_weight         288.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8804(5)
_cell_length_b                   7.0690(3)
_cell_length_c                   22.5844(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.420(2)
_cell_angle_gamma                90
_cell_volume                     1415.22(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3385
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1539 before and 0.0798 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12831
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.418
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2190
_reflns_number_total             3240
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.10-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.4505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C15(H15), C13(H13), C3(H3), C19(H19), C5(H5), C16(H16),
 C4(H4), C18(H18), C17(H17)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.93941(14) 0.24681(19) 0.45836(6) 0.0349(3) Uani 1 1 d . . . . .
N2 N 0.54574(16) 0.3019(2) 0.41678(7) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.73640(16) 0.2148(2) 0.51382(6) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.48246(19) 0.2732(2) 0.47141(8) 0.0272(4) Uani 1 1 d . . . . .
C10 C 0.69927(19) 0.2858(2) 0.40965(8) 0.0268(4) Uani 1 1 d . . . . .
C11 C 0.7248(2) 0.3199(2) 0.35041(8) 0.0287(4) Uani 1 1 d . . . . .
C9 C 0.8016(2) 0.2491(2) 0.46088(8) 0.0265(4) Uani 1 1 d . . . . .
C7 C 0.8389(2) 0.1560(3) 0.56404(8) 0.0288(4) Uani 1 1 d . . . . .
H7A H 0.928248 0.093553 0.548508 0.035 Uiso 1 1 calc R U . . .
H7B H 0.786906 0.062000 0.588089 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8644(2) 0.3076(3) 0.31902(8) 0.0306(4) Uani 1 1 d . . . . .
C2 C 0.3281(2) 0.2852(3) 0.47729(9) 0.0343(5) Uani 1 1 d . . . . .
H2 H 0.262608 0.313193 0.443639 0.041 Uiso 1 1 calc R U . . .
C6 C 0.58021(19) 0.2293(2) 0.52042(8) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.5814(2) 0.3617(3) 0.32240(9) 0.0366(5) Uani 1 1 d . . . . .
H12 H 0.562520 0.393409 0.281760 0.044 Uiso 1 1 calc R U . . .
C15 C 0.9714(2) 0.1664(3) 0.33215(8) 0.0334(4) Uani 1 1 d . . . . .
H15 H 0.955593 0.079303 0.363206 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4754(2) 0.3489(3) 0.36323(9) 0.0363(5) Uani 1 1 d . . . . .
H13 H 0.370170 0.369096 0.355841 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2694(2) 0.2567(3) 0.53171(10) 0.0384(5) Uani 1 1 d . . . . .
H3 H 0.163621 0.264798 0.535489 0.046 Uiso 1 1 calc R U . . .
C19 C 0.8914(2) 0.4303(3) 0.27271(9) 0.0401(5) Uani 1 1 d . . . . .
H19 H 0.820216 0.526948 0.262399 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5185(2) 0.2025(3) 0.57531(9) 0.0330(4) Uani 1 1 d . . . . .
H5 H 0.583049 0.174394 0.609232 0.040 Uiso 1 1 calc R U . . .
C8 C 0.8913(2) 0.3195(3) 0.60363(9) 0.0354(5) Uani 1 1 d . . . . .
H8A H 0.937282 0.416980 0.579672 0.053 Uiso 1 1 calc R U . . .
H8B H 0.965727 0.273913 0.634109 0.053 Uiso 1 1 calc R U . . .
H8C H 0.804705 0.373313 0.622676 0.053 Uiso 1 1 calc R U . . .
C16 C 1.0995(2) 0.1511(3) 0.30086(9) 0.0388(5) Uani 1 1 d . . . . .
H16 H 1.170869 0.054325 0.310706 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3646(2) 0.2163(3) 0.58086(10) 0.0385(5) Uani 1 1 d . . . . .
H4 H 0.324233 0.198051 0.618454 0.046 Uiso 1 1 calc R U . . .
C18 C 1.0203(3) 0.4142(3) 0.24129(9) 0.0469(6) Uani 1 1 d . . . . .
H18 H 1.036573 0.499640 0.209840 0.056 Uiso 1 1 calc R U . . .
C17 C 1.1248(2) 0.2751(3) 0.25542(10) 0.0437(5) Uani 1 1 d . . . . .
H17 H 1.213476 0.264675 0.234078 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.229(2) . ?
N2 C1 1.401(2) . ?
N2 C10 1.387(2) . ?
N2 C13 1.369(2) . ?
N1 C9 1.380(2) . ?
N1 C7 1.472(2) . ?
N1 C6 1.408(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.400(2) . ?
C10 C11 1.391(3) . ?
C10 C9 1.451(2) . ?
C11 C14 1.467(3) . ?
C11 C12 1.419(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.391(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C6 C5 1.398(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.360(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.378(3) . ?
C4 H4 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.377(3) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C1 122.63(15) . . ?
C13 N2 C1 128.86(15) . . ?
C13 N2 C10 108.51(16) . . ?
C9 N1 C7 116.41(14) . . ?
C9 N1 C6 123.08(15) . . ?
C6 N1 C7 120.49(15) . . ?
C2 C1 N2 121.73(17) . . ?
C2 C1 C6 120.48(18) . . ?
C6 C1 N2 117.78(15) . . ?
N2 C10 C11 108.38(15) . . ?
N2 C10 C9 119.68(16) . . ?
C11 C10 C9 131.86(17) . . ?
C10 C11 C14 130.20(17) . . ?
C10 C11 C12 105.73(17) . . ?
C12 C11 C14 123.98(17) . . ?
O1 C9 N1 120.55(16) . . ?
O1 C9 C10 122.91(16) . . ?
N1 C9 C10 116.54(15) . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
N1 C7 C8 113.12(15) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C15 C14 C11 121.57(17) . . ?
C19 C14 C11 120.96(17) . . ?
C19 C14 C15 117.37(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.33(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C6 N1 120.05(16) . . ?
C5 C6 N1 121.67(16) . . ?
C5 C6 C1 118.28(16) . . ?
C11 C12 H12 125.6 . . ?
C13 C12 C11 108.86(17) . . ?
C13 C12 H12 125.6 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.23(18) . . ?
C16 C15 H15 119.4 . . ?
N2 C13 H13 125.7 . . ?
C12 C13 N2 108.50(16) . . ?
C12 C13 H13 125.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.97(18) . . ?
C4 C3 H3 120.0 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.17(19) . . ?
C18 C19 H19 119.4 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.83(18) . . ?
C4 C5 H5 119.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.09(19) . . ?
C5 C4 H4 120.0 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -179.81(16) . . . . ?
N2 C1 C6 N1 -0.2(2) . . . . ?
N2 C1 C6 C5 179.29(15) . . . . ?
N2 C10 C11 C14 -175.22(17) . . . . ?
N2 C10 C11 C12 1.36(19) . . . . ?
N2 C10 C9 O1 -174.59(16) . . . . ?
N2 C10 C9 N1 5.8(2) . . . . ?
N1 C6 C5 C4 -179.65(16) . . . . ?
C1 N2 C10 C11 179.15(15) . . . . ?
C1 N2 C10 C9 -3.8(2) . . . . ?
C1 N2 C13 C12 -179.91(17) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C5 C4 0.9(3) . . . . ?
C10 N2 C1 C2 -178.33(16) . . . . ?
C10 N2 C1 C6 1.0(2) . . . . ?
C10 N2 C13 C12 0.3(2) . . . . ?
C10 C11 C14 C15 37.3(3) . . . . ?
C10 C11 C14 C19 -146.3(2) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C11 C10 C9 O1 1.6(3) . . . . ?
C11 C10 C9 N1 -178.02(17) . . . . ?
C11 C14 C15 C16 177.40(18) . . . . ?
C11 C14 C19 C18 -177.32(19) . . . . ?
C11 C12 C13 N2 0.5(2) . . . . ?
C9 N1 C7 C8 95.05(18) . . . . ?
C9 N1 C6 C1 2.5(2) . . . . ?
C9 N1 C6 C5 -176.92(16) . . . . ?
C9 C10 C11 C14 8.3(3) . . . . ?
C9 C10 C11 C12 -175.16(18) . . . . ?
C7 N1 C9 O1 -6.5(2) . . . . ?
C7 N1 C9 C10 173.13(15) . . . . ?
C7 N1 C6 C1 -175.75(15) . . . . ?
C7 N1 C6 C5 4.8(2) . . . . ?
C14 C11 C12 C13 175.68(17) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C19 C18 C17 0.1(3) . . . . ?
C2 C1 C6 N1 179.11(15) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C6 N1 C9 O1 175.14(16) . . . . ?
C6 N1 C9 C10 -5.2(2) . . . . ?
C6 N1 C7 C8 -86.54(19) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C12 C11 C14 C15 -138.76(19) . . . . ?
C12 C11 C14 C19 37.7(3) . . . . ?
C15 C14 C19 C18 -0.7(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C13 N2 C1 C2 2.0(3) . . . . ?
C13 N2 C1 C6 -178.76(17) . . . . ?
C13 N2 C10 C11 -1.08(19) . . . . ?
C13 N2 C10 C9 175.94(15) . . . . ?
C19 C14 C15 C16 0.8(3) . . . . ?
C19 C18 C17 C16 0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
